The Keeping Up with the Kardashians regular has been dating the matriarch of the family since 2014, but fans (and the Kardashian-Jenner siblings) still don't know much about the 38-year-old

By Diane J. Cho
September 08, 2019 02:00 PM
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After five years of dating Kris Jenner and appearing on numerous episodes of Keeping Up with the Kardashians, Corey Gamble has somehow remained shrouded in mystery. Gamble’s preference to keep all aspects of his life and relationship with Jenner, 63, private was a hot topic during last season of Keeping Up, and the new season 17 trailer, which reveals an explosive scene between Scott Disick and Gamble, has only piqued fans’ interest even more.

Although a source told PEOPLE in 2017 that Jenner and Gamble “will never get married,” the 38-year-old is still considered Jenner’s “ride or die,” so it’s time for fans to learn more about who Gamble is and how he’s been able to maintain his man of mystery status.

Gamble Is Originally from Atlanta

He attended Westlake High School, in the class of 1999, and went to Morehouse College to study business marketing, according to his Facebook page.

He Was Working for Scooter Braun When He Met Jenner

Gamble was serving as Justin Bieber’s tour manager when he and Jenner first began their romance after meeting at fashion designer Riccardo Tisci’s 40th birthday bash in Ibiza, Spain.

He Doesn’t Drink or Party a Lot, Despite His Lavish Lifestyle

Dating Jenner must mean endless parties, galas and vacations, but a source once told E! that Gamble is a lot more low-key than fans think. “He’s a really great guy,” a source told the outlet. “He’s so nice and a very responsible man. He doesn’t drink or party. He is very caring about other people and generally just an all-around good guy.”

The whole not drinking thing might have changed, based on this Instagram post from 2016, but him being a caring guy has seemingly remained the same.

“Happy Birthday to my Ride or Die!!! You are amazing babe @Coreygamble I love you!!,” Jenner gushed on Instagram in 2018. “Thank you for everything you do for all of us… you are always holding it down. #love #HBcorey!!!”

Motivational Quotes Keep Him Going

One look at his Instagram and it’s obvious that Gamble is a go-getter who uses motivational quotes and mantras to fuel his work ethic.

He Has Many Friends in High Places

The music entrepreneur has many famous, highly successful friends including designer Tommy Hilfiger, hospitality entrepreneur David Grutman and Hillsong pastor Carl Lentz.

Gamble’s Relationship with Jenner’s Kids Didn’t Have the Smoothest Start

While the couple was enjoying their honeymoon phase, Jenner’s daughters expressed concern over their mother’s new relationship very early on, calling their age difference “creepy.” (Gamble and Jenner are 25 years apart.)

Confronted by her daughter’s questions, Jenner told KUWTK cameras back in 2014: “It’s so annoying that my own family is being so judgmental because all I really want to do is live my life.”

Jenner’s Son-in-Law, Kanye West, Also Expressed Concern

The drama surrounding Gamble picked back up again on the last season of KUWTK after West threw shade at Gamble via text, questioning why the Kardashian-Jenner family had never met Gamble’s family.

“Kanye texts Corey something along the lines of, ‘Look, we don’t know you, we’ve never met any of your family members,’ ” explained Kim, as Disick, Kourtney and Khloé met with Jenner to discuss the matter during season 16. “Of course we’ve all felt that way and thought that, but for Kanye to just so bluntly say that to him — I feel like that was the wrong choice to make at that time.”

“Kanye’s delivery wasn’t great, but the essence of what he said is true,” Khloé added. “Corey does tend to be pretty secretive and that does have me pretty guarded. … We don’t know Corey like that.”

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Credit: Kris Jenner/Instagram

She even admitted that she never thought the relationship would go the distance.

“After my mom got her divorce, I was like, ‘Okay, this probably isn’t going to last,’ ” Khloé said. “I just didn’t feel the need to get that connected or attached. Then when I saw time progressing and the relationship was still there, we tried to get to know him, but he has not been receptive in this whole thing.”

Kardashian-Jenner Family Photo
Credit: Kendall Jenner/Instagram

Gamble Has Been Able to Protect His Private Life While Being Part of the Family, Thanks to Jenner and Her Support

After the Kardashian-Jenner kids and West voiced their opinions of Gamble and why he has chosen to keep things from the family, Jenner came through to defend her man.

“Nobody really slows down enough to take a look at it from a bird’s eye view of my life,” Jenner told Khloé during a mother-daughter heart to heart. “I want you to recognize that when you do question my relationship with Corey, it isn’t okay and it hurts feelings. I think what you guys don’t realize is Corey is really taking care of me like no one ever has in my entire life.”

With that, Khloé backed down.

“I want you to be happy,” she said. “And I don’t care who you’re with as long as they’re good to you. … You have to live your life for you and be happy and if you are, that’s great. I support you and I want you to feel like we’re happy for you, because we are.”

Feeling guilty, Khloé recruited Kim to apologize to Gamble, who insisted he just wants to stay on the “peace train.”

“We’re happy you make our mom happy,” Khloé said. “We just want to move forward and be in a good place.”

“Ultimately, we just want to protect my mom,” Kim added. “She’s always going to be the most important thing to us so we are going to do what we can to just look out for her.”